Vinyl monomers bearing chromophore moieties and their polymers. VIII. synthesis and fluorescence behavior of a vinyloxy monomer having an electron-accepting chromophore moiety, p-((vinyloxy)methyl)benzonitrile, and its polymers

✍ Scribed by Fu-Sheng Du; Zi-Chen Li; Fu-Mian Li

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 188 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990115)37:2<179::aid-pola8>3.0.co;2-4

✦ Synopsis

A vinyloxy monomer having an electron-accepting chromophore moiety, p-((vinyloxy)methyl)benzonitrile (VOMBN), was synthesized by reaction of p-(hydroxymethyl)benzonitrile with ethyl vinyl ether (EVE) in the presence of mercuric acetate. VOMBN can easily be cationically homopolymerized and copolymerized with EVE by using Lewis acids such as boron trifluoride etherate (BF 3 ⅐ OEt 2 ) as a catalyst and radically copolymerized with maleic anhydride (MAn) using AIBN as an initiator. The fluorescence behaviors of VOMBN, its copolymer P(VOMBN-co-MAn), and its saturated model compound p-(ethoxymethyl)benzonitrile (EOMBN) were investigated in acetonitrile. It has been found that the fluorescence intensity of VOMBN is much lower than its copolymer and EOMBN at the same chromophore concentration. A fluorescence "structural self-quenching effect" (SSQE) is also observed for VOMBN as we have reported previously [Li, F.